Transfer Between iPods...

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So I have a Classic which I hold all of my music on and I have a Nano for on the go. I recently deleted all the music off of my laptop (too much space taken up) and now keep it solely on my Classic.

Question:
How can I transfer songs from my Classic to my Nano? I can't drag and drop between them in iTunes... is there any freeware anyone knows of to help solve this?

Thanks
 
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20" Intel iMac 2.4 Ghz/3G Ram/320HD, Snow Leopard. PBook G4, 1.5Ghz/1.5 Ram/250 HD, Leopard 10.5.6.
The only way I can think of is to rip it back to iTunes and then sync your nano to that.
Try some freeware called iPod rip. It's only free for 10 uses, but it's good, and preserves tags etc.
You should find it on www.versiontracker.com.
 
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Senuti is perfect for that ... you can plug in your iPod and if iTunes launches just quit it. Then launch Senuti and just select all tracks and click the Transfer button and the songs will be saved to your Hard Drive in a specified folder.

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